ChemicalBook CAS DataBase List Fmoc-Orn(Boc)-OH

Fmoc-Orn(Boc)-OH synthesis

8synthesis methods

Product Name:Fmoc-Orn(Boc)-OH
CAS Number:109425-55-0
Molecular formula:C25H30N2O6
Molecular Weight:454.52

2 mmol L-Orn was weighted and dissolved in 15 ml of acetonitrile; 16 mmol Boc2O was dissolved in acetonitrile and added dropwise to an acetonitrile solution of ornithine, to react and generate a complex; 10 ml 20% sodium bicarbonate aqueous solution was added, and 2 g of anhydrous sodium carbonate and an appropriate amount of 8-hydroxyquinoline were added in batches; the mixture was stirred and reacted at room temperature for 4 hours to remove copper ions in the complex; then 2 mmol Fmoc-OSu was added to the aforesaid solution, followed by stirring at room temperature for 2 hours; the resultant was recrystallized with an ethyl acetate/petroleum ether mixed solvent, to obtain a peptide head intermediate Fmoc-Orn(Boc)-OH.
Nalpha-Fmoc-Ndelta-Boc-L-ornithine

70-26-8
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24424-99-5 Synthesis

24424-99-5
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82911-69-1 Synthesis

N-(9-Fluorenylmethoxycarbonyloxy)succinimide

82911-69-1
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109425-55-0
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Yield:-

Reaction Conditions:

Stage #1: L-ornithine;di-tert-butyl dicarbonatewith 8-quinolinol;sodium hydrogencarbonate;sodium carbonate in water;acetonitrile at 20; for 4 h;
Stage #2: N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide in water;acetonitrile at 20; for 2 h;Temperature;

Steps:

1.1 Example 1

2 mmol L-Orn was weighted and dissolved in 15 ml of acetonitrile; 16 mmol Boc₂O was dissolved in acetonitrile and added dropwise to an acetonitrile solution of ornithine, to react and generate a complex; 10 ml 20% sodium bicarbonate aqueous solution was added, and 2 g of anhydrous sodium carbonate and an appropriate amount of 8-hydroxyquinoline were added in batches; the mixture was stirred and reacted at room temperature for 4 hours to remove copper ions in the complex; then 2 mmol Fmoc-OSu was added to the aforesaid solution, followed by stirring at room temperature for 2 hours; the resultant was recrystallized with an ethyl acetate/petroleum ether mixed solvent, to obtain a peptide head intermediate Fmoc-L-Orn (Boc)-OH.

References:

US2017/355667,2017,A1 Location in patent:Paragraph 0059; 0069; 0073; 0085